Toluene → Methyl 3-methoxy-2-oxocyclopentane-1-carboxylate

HRID 579740Notes

Reaction equation

HRID 579740 reaction equation
[Na].C1(C)C=CC=CC=1.[CH3:9][O:10][CH:11]([CH2:16][CH2:17][CH2:18][C:19]([O:21][CH3:22])=[O:20])[C:12]([O:14]C)=O>C(O)(=O)C>[CH3:9][O:10][CH:11]1[CH2:16][CH2:17][CH:18]([C:19]([O:21][CH3:22])=[O:20])[C:12]1=[O:14]

Participants

5

Reactant 3

HCID 1140TolueneHCID 589322HCID 589322, compoundHCID 5360545Sodium

Product 1

HCID 14231087Methyl 3-methoxy-2-oxocyclopentane-1-carboxylateYield 54.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

1.38 g of sodium metal was added to 100 ml of toluene, and the mixture was heated to 60° C. 10.2 g of dimethyl α-methoxyadipate [prepared as described in step (a) above] were then added dropwise to the hot mixture. The mixture was then heated under reflux for 8 hours, after which it was cooled to room temperature and added to a 10% w/v aqueous solution of acetic acid. The organic layer was separated, washed first with a saturated aqueous solution of sodium carbonate and then with water, and then dried over anhydrous sodium sulfate. The solvent was then evaporated off under reduced pressure, and the residue was distilled, to give 4.66 g of the title compound as a pale oil, boiling at 83°-87° C./3 mm Hg (about 400 Pa).

Workup

  1. temperatureThe mixture was then heated
  2. temperatureunder reflux for 8 hours
  3. temperatureafter which it was cooled to room temperature
  4. customThe organic layer was separated
  5. washwashed first with a saturated aqueous solution of sodium carbonate
  6. dry with materialwith water, and then dried over anhydrous sodium sulfate
  7. customThe solvent was then evaporated off under reduced pressure
  8. distillationthe residue was distilled

Sources & evidence

ORD record
ord-6c51a226be0a466688fa50fe53848119
Source dataset
uspto-grants-1988_06
Patent number
US04749704

Reaction notes

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